Well there's the rub, right? If it's a problem upstream of the junction on the axle, it should work against both calipers. But perhaps, the driver's side being the short side, there's just enough to exert pressure there, but not the other side?
Never heard of such a thing, as it's supposed to be equal throughout the system, BUT, I run into a lot of things I've never heard of or experienced before. Once you find that, it becomes experience. But before that, it's a puzzlement.
A single bad hose maybe?
Debris in that hard line? Seems unlikely as most buildup of junk or rust would effect pressure both ways I would think. You'd see it also as a pull to one side when that caliper is not getting full pressure.
But here again, stranger things have happened.%)
Too bad you don't have someone you can swap calipers and other components with temporarily. Yeah, that's a lot of work to trace a problem, but at least you could eliminate pieces one by one without spending any money.
How about next time it does it, loosen the fittings one position further up?
When you run into a fitting that does not release the pressure, you might be on to something. Even to the point of loosening the nuts that hold the master to the firewall, to let it pull forward off the pedal. It's always possible that the pedal is putting pressure on the system, but the driver's side is more sensitive to it.
Also, while still working with components down on the axle, don't forget to open up the bleeder on the opposite caliper, to see if that also releases the pressure on the driver's side.
Maybe the reason it's only one side is that the passenger side is a little sticky and takes more pressure to hold against the rotor.
Good luck.
Paul